Vinorelbine tartrate
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MedKoo CAT#: 100930

CAS#: 125317-39-7 (tartrate)

Description: Vinorelbine is a semisynthetic vinca alkaloid derived from the leaves of the periwinkle plant (Vinca rosea) with antineoplastic activity. Vinorelbine binds to tubulin, thereby inhibiting tubulin polymerization into microtubules and spindle formation and resulting in apoptosis of susceptible cancer cells. Inhibition of mitotic microtubules correlates with antitumor activity, whereas inhibition of axonal microtubules seems to correlate with vinorelbine's neurotoxicity. Compared to related vinca alkaloids, vinorelbine is more selective against mitotic than axonal microtubules in vitro, which may account for its decreased neurotoxicity. This agent is also a radiation-sensitizing agent.


Chemical Structure

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Vinorelbine tartrate
CAS# 125317-39-7 (tartrate)

Theoretical Analysis

MedKoo Cat#: 100930
Name: Vinorelbine tartrate
CAS#: 125317-39-7 (tartrate)
Chemical Formula: C53H66N4O20
Exact Mass: 1078.42704
Molecular Weight: 1079.1
Elemental Analysis: C, 58.99; H, 6.16; N, 5.19; O, 29.65

Price and Availability

Size Price Availability Quantity
50.0mg USD 90.0 Same day
100.0mg USD 150.0 Same day
200.0mg USD 250.0 Same day
500.0mg USD 450.0 Same day
1.0g USD 750.0 Same day
2.0g USD 1250.0 Same day
5.0g USD 1950.0 Same day
10.0g USD 2950.0 2 weeks
20.0g USD 4650.0 2 weeks
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Related CAS #: 125317-39-7 (tartrate)   105661-07-2 (tartrate 1:1)   71486-22-1 (free base)    

Synonym: KW2307, KW-2307, KW 2307, vinorelbine tartrate, Navelbine, Biovelbin, Eunades

IUPAC/Chemical Name: methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis((2R,3R)-2,3-dihydroxysuccinate)

InChi Key: CILBMBUYJCWATM-PYGJLNRPSA-N

InChi Code: InChI=1S/C45H54N4O8.2C4H6O6/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7;2*5-1(3(7)8)2(6)4(9)10/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t28-,37-,38+,39+,42+,43+,44-,45-;2*1-,2-/m011/s1

SMILES Code: O=C(OC)[C@@]1([C@@]2(N(C3=C([C@@]24CCN5CC=C[C@@](CC)([C@H]1OC(C)=O)[C@@]45[H])C=C(C(OC)=C3)[C@]6(C[C@]7([H])C=C(CN(CC8=C6NC9=C8C=CC=C9)C7)CC)C(OC)=O)C)[H])O.O=C([C@@H]([C@H](C(O)=O)O)O)O.O=C([C@@H]([C@H](C(O)=O)O)O)O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Vinorelbine (ditartrate) inhibits the proliferation of Hela cells with IC50 of 1.25 nM.
In vitro activity: To determine the mechanism of protection from the pro-apoptotic action of metronomic vinorelbine the balance of the anti-apoptotic Bcl-2 and pro-apoptotic protein Bax (Fig. 6A) was investigated. Bcl-2 and Bax are players of the intrinsic mitochondrial apoptotic pathway and a low Bcl-2/Bax ratio leads to apoptotic cell death through mitochondrial outer membrane permeabilization (MOMP). Moreover, Bcl-2 downregulation has previously been implicated in the cell death caused by vinorelbine. Ten nanomolar vinorelbine downregulated the anti-apoptotic protein Bcl-2 in normoxia by 32% (P<0.01) at 24 h. Severe hypoxia also decreased Bcl-2 protein by 46% (P<0.001) but 10 nM vinorelbine did not further reduce Bcl-2 under these conditions (Fig. 6B). Similar changes were seen in the Bcl-2/Bax ratio (Fig. 6C). In particular, 10 nM vinorelbine decreased the Bcl-2/Bax ratio by 30% (P<0.05) in normoxia at 24 h, which is consistent with induction of apoptosis. Severe hypoxia decreased the Bcl-2/Bax ratio by 42% (P<0.01) while 10 nM vinorelbine did not have an additional effect. Reference: Int J Oncol. 2015 Aug; 47(2): 455–464. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4501653/
In vivo activity: This study used a model previously described where JEG3 cells are xenografted subcutaneously into immune deficient (SCID) female mice and placental tumors allowed to form. Mice were then treated intravenously (via tail vein) with 1.25, 2.5 or 5 mg/kg vinorelbine, or vehicle control on days 6, 9 and 12 after xenograft inoculation. Compared to vehicle controls, vinorelbine at all doses significantly reduced xenograft volume 4 days after treatment (10 days after JEG3 inoculation) and each measured time point thereafter (12 and 14 days after inoculation) (Fig. 2A, B). Furthermore, vinorelbine treatment caused a significant, dose dependent reduction in xenograft tumor weight (harvested at the time of euthanasia) (Fig. 2C). There was a concordant dose dependent reduction in serum hCG from blood taken at the time of euthanasia. Significantly, at the top dose of vinorelbine (5 mg/kg) 6 out of 8 mice had a resolution of the tumor to the extent that no tumor could be found (Fig. 2C). Of these 6 mice, 5 had serum hCG levels below the detectable range of the assay (Fig. 2D). This suggests the possible complete absence of placental xenograft tumors in 5 mice. Reference: EBioMedicine. 2018 Mar; 29: 166–176. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5925452/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 92.67
Ethanol 100.0 92.67
Water 100.0 92.67

Preparing Stock Solutions

The following data is based on the product molecular weight 1079.1 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Mavroeidis L, Sheldon H, Briasoulis E, Marselos M, Pappas P, Harris AL. Metronomic vinorelbine: Anti-angiogenic activity in vitro in normoxic and severe hypoxic conditions, and severe hypoxia-induced resistance to its anti-proliferative effect with reversal by Akt inhibition. Int J Oncol. 2015 Aug;47(2):455-64. doi: 10.3892/ijo.2015.3059. Epub 2015 Jun 19. PMID: 26095084; PMCID: PMC4501653. 2. Thomas-Schoemann A, Lemare F, Mongaret C, Bermudez E, Chéreau C, Nicco C, Dauphin A, Weill B, Goldwasser F, Batteux F, Alexandre J. Bystander effect of vinorelbine alters antitumor immune response. Int J Cancer. 2011 Sep 15;129(6):1511-8. doi: 10.1002/ijc.25813. Epub 2011 Apr 1. PMID: 21128224. 3. Hastie R, Lim E, Sluka P, Campbell L, Horne AW, Ellett L, Hannan NJ, Brownfoot F, Kaitu'u-Lino TJ, Tong S. Vinorelbine Potently Induces Placental Cell Death, Does Not Harm Fertility and is a Potential Treatment for Ectopic Pregnancy. EBioMedicine. 2018 Mar;29:166-176. doi: 10.1016/j.ebiom.2018.01.041. Epub 2018 Feb 2. PMID: 29429891; PMCID: PMC5925452. 4. Cui R, Yoshioka M, Takahashi F, Ishida H, Iwakami S, Takahashi K. Vinorelbine is effective for the malignant pleural effusion associated with lung cancer in mice. Anticancer Res. 2008 May-Jun;28(3A):1633-9. PMID: 18630520.
In vitro protocol: 1. Mavroeidis L, Sheldon H, Briasoulis E, Marselos M, Pappas P, Harris AL. Metronomic vinorelbine: Anti-angiogenic activity in vitro in normoxic and severe hypoxic conditions, and severe hypoxia-induced resistance to its anti-proliferative effect with reversal by Akt inhibition. Int J Oncol. 2015 Aug;47(2):455-64. doi: 10.3892/ijo.2015.3059. Epub 2015 Jun 19. PMID: 26095084; PMCID: PMC4501653. 2. Thomas-Schoemann A, Lemare F, Mongaret C, Bermudez E, Chéreau C, Nicco C, Dauphin A, Weill B, Goldwasser F, Batteux F, Alexandre J. Bystander effect of vinorelbine alters antitumor immune response. Int J Cancer. 2011 Sep 15;129(6):1511-8. doi: 10.1002/ijc.25813. Epub 2011 Apr 1. PMID: 21128224.
In vivo protocol: 1. Hastie R, Lim E, Sluka P, Campbell L, Horne AW, Ellett L, Hannan NJ, Brownfoot F, Kaitu'u-Lino TJ, Tong S. Vinorelbine Potently Induces Placental Cell Death, Does Not Harm Fertility and is a Potential Treatment for Ectopic Pregnancy. EBioMedicine. 2018 Mar;29:166-176. doi: 10.1016/j.ebiom.2018.01.041. Epub 2018 Feb 2. PMID: 29429891; PMCID: PMC5925452. 2. Cui R, Yoshioka M, Takahashi F, Ishida H, Iwakami S, Takahashi K. Vinorelbine is effective for the malignant pleural effusion associated with lung cancer in mice. Anticancer Res. 2008 May-Jun;28(3A):1633-9. PMID: 18630520.

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12: Passardi A, Fanini F, Turci L, Foca F, Rosetti P, Ruscelli S, Casadei Gardini A, Valgiusti M, Dazzi C, Marangolo M. Prolonged Pemetrexed Infusion Plus Gemcitabine in Refractory Metastatic Colorectal Cancer: Preclinical Rationale and Phase II Study Results. Oncologist. 2017 Jun 7. pii: theoncologist.2017-0206. doi: 10.1634/theoncologist.2017-0206. [Epub ahead of print] PubMed PMID: 28592624.

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16: Suda K, Rozeboom L, Rivard CJ, Yu H, Ellison K, Melnick MAC, Hinz TK, Chan D, Heasley LE, Politi K, Mitsudomi T, Hirsch FR. Therapy-induced E-cadherin downregulation alters expression of programmed death ligand-1 in lung cancer cells. Lung Cancer. 2017 Jul;109:1-8. doi: 10.1016/j.lungcan.2017.04.010. Epub 2017 Apr 19. PubMed PMID: 28577937.

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18: Gadgeel SM. Role of Chemotherapy and Targeted Therapy in Early-Stage Non-Small Cell Lung Cancer. Am Soc Clin Oncol Educ Book. 2017;37:630-639. doi: 10.14694/EDBK_175188. PubMed PMID: 28561669.

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20: Montagna E, Vingiani A, Maisonneuve P, Cancello G, Contaldo F, Pruneri G, Colleoni M. Unfavorable prognostic role of tumor-infiltrating lymphocytes in hormone-receptor positive, HER2 negative metastatic breast cancer treated with metronomic chemotherapy. Breast. 2017 Aug;34:83-88. doi: 10.1016/j.breast.2017.05.009. Epub 2017 May 23. PubMed PMID: 28544923.



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